bis(4-formylbenzyl)ammonium hexafluorophosphate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(4-formylbenzyl)ammonium hexafluorophosphate
• 英文别名: Bis[(4-formylphenyl)methyl]azanium;hexafluorophosphate
• 化学式: C₁₆H₁₅NO₂*F₆P*H
• 分子量: 399.273
• InChiKey: DQNSGPUOJYCCLY-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  bis(4-formylbenzyl)ammonium hexafluorophosphate 、 3,5-二叔丁基苯胺 在 苯硒酚 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  Rotaxane Formation under Thermodynamic Control

  摘要：

  [GRAPHICS]Thermodynamic control operates in the synthesis of a [2]rotaxane based upon the dibenzylammonium ion/crown ether recognition motif, When dibenzo[24]crown-8 is added to an acetonitrile solution containing a diimine dumbbell-like component, the dynamic nature of the system (i.e., imine hydrolysis/reformation) offers the ring component access to the NH2+ center, allowing the self-assembly of the corresponding "dynamic" [2]rotaxane to occur. The "fixing" of this [2]rotaxane can be achieved upon reduction of the imine bonds, affording a kinetically inert [2]rotaxane.

  DOI：

  10.1021/ol990966j
• 作为产物：
  描述：

  4-[[(4-Formylphenyl)methylamino]methyl]benzaldehyde 在 ammonium hexafluorophosphate 作用下， 以 水 为溶剂， 生成 bis(4-formylbenzyl)ammonium hexafluorophosphate
  参考文献：
  名称：

  Computationally forecasting the effect of dibenzylammonium substituents on pseudorotaxane formation with dibenzo[24]crown-8

  摘要：

  The ability to predict the relative stabilities of analogous pseudorotaxanes is essential for the synthetic chemist yet simplified computational forecasting approaches remain scarce. Consequently, ten [2]pseudorotaxanes have been assembled (from a series of para-substituted dibenzylammonium ions and dibenzo[24]crown-8) and their experimentally-determined stabilities correlated with two computational parameters closely related to complexation energy. The strongest relationship was obtained from density functional theory calculation of binding energy (R-2 = 0.92) while determination of the maximum surface electrostatic potential on the dibenzylammonium ions (a proxy indicator of complex stability) afforded comparable results (R-2 = 0.88) with great reduction in computational expense. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.061

文献信息

• Locking the Dynamic Axial Chirality of Biphenyl Crown Ethers through Threading
  作者：Tomoya Kimura、Shinobu Miyagawa、Hikaru Takaya、Masaya Naito、Yuji Tokunaga

  DOI：10.1002/asia.202001046

  日期：2020.11.16

  comprising 23‐ and 26‐membered biphenyl crown ethers as the macrocyclic components and secondary ammonium ions as the dumbbell‐shaped components, and the locking of the dynamic axial chirality of the biphenyl moieties in these structures. Chiral high‐performance liquid chromatography (HPLC) revealed that our [2]rotaxane featuring the 26‐membered crown ether racemized at room temperature, but the racemization

  本文描述了由23和26元联苯冠醚作为大环组分，仲铵离子作为哑铃状组分的[2]轮烷的合成，以及这些结构中联苯部分的动态轴向手性的锁定。手性高效液相色谱法（HPLC）显示，具有26元冠醚的[2]轮烷在室温下外消旋，但具有23元冠醚的[2]轮烷的外消旋在室温下未进行在三天内。通过手性HPLC分离并结合了23元冠醚的[2]轮烷的对映异构体后，我们研究了其在高温下的外消旋作用。在二甲亚砜（一种极性溶剂）中的立体转化速度要快于在o-二氯苯（一种非极性溶剂），在这里我们讨论这些动力学参数。
• Efficient Solvent-Free Syntheses of [2]- and [4]Rotaxanes
  作者：Sheng-Yao Hsueh、Kuang-Wei Cheng、Chien-Chen Lai、Sheng-Hsien Chiu

  DOI：10.1002/anie.200800530

  日期：2008.5.26
• Modular construction of pyrido[24]crown-8-based templates in the self-assembly of cross-linked [n]catenanes
  作者：Luke C. Delmas、Nicholas A. Payne、Franklyn Julien、Avril R. Williams

  DOI：10.1016/j.tetlet.2017.07.006

  日期：2017.8

  Starting from the versatile 4-bromopyrido[24]crown-8 building block, novel ditopic and tritopic receptors have been synthesized and shown to be appropriate hosts for bis(4-formylbenzyl)ammonium hexafluorophosphate. Association constants (per binding site) for the corresponding [3]- and [4]pseudorotaxanes, assembled from these components, were determined to be 2753 M-1 and 723 M-1, respectively. Mechanical bond formation was attempted utilizing dynamic imine bond formation between the formyl groups of the bound dibenzylammonium threads and p-phenylenediamine. (C) 2017 Elsevier Ltd. All rights reserved.
• Bromopyrido-24-crown-8: a versatile building block for the construction of interlocked molecules
  作者：Luke C. Delmas、Nicholas A. Payne、Avril R. Williams

  DOI：10.1016/j.tetlet.2015.11.105

  日期：2016.2

  The usefulness of the aryl halide, 4-bromopyrido-24-crown-8, in easily appending the pyrido-24-crown-8 unit onto organic frameworks to afford new dibenzylammonium receptors has been explored. Bromopyrido-24-crown-8 has been coupled with phenylboronic acid to yield 4-phenylpyrido-24-crown-8, which is shown to complex a variety of dibenzylammonium ions yielding complexes that are more stable than their dibenzo-24-crown-8 counterparts. One of these new complexes, in which a diformyl-terminated thread is bound, has been used to assemble a [2]rotaxane under thermodynamic control. (C) 2015 Elsevier Ltd. All rights reserved.
• Computationally forecasting the effect of dibenzylammonium substituents on pseudorotaxane formation with dibenzo[24]crown-8
  作者：Nicholas A. Payne、Luke C. Delmas、Sean A.C. McDowell、Avril R. Williams

  DOI：10.1016/j.tetlet.2015.07.061

  日期：2015.9

  The ability to predict the relative stabilities of analogous pseudorotaxanes is essential for the synthetic chemist yet simplified computational forecasting approaches remain scarce. Consequently, ten [2]pseudorotaxanes have been assembled (from a series of para-substituted dibenzylammonium ions and dibenzo[24]crown-8) and their experimentally-determined stabilities correlated with two computational parameters closely related to complexation energy. The strongest relationship was obtained from density functional theory calculation of binding energy (R-2 = 0.92) while determination of the maximum surface electrostatic potential on the dibenzylammonium ions (a proxy indicator of complex stability) afforded comparable results (R-2 = 0.88) with great reduction in computational expense. (C) 2015 Elsevier Ltd. All rights reserved.